Ustiloxin A
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| Category | Antibiotics |
| Catalog number | BBF-02740 |
| CAS | 143557-93-1 |
| Molecular Weight | 673.73 |
| Molecular Formula | C28H43N5O12S |
| Purity | ≥95% |
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Description
It is originally isolated from Ustilaginoidea virens. Ustiloxin A can inhibit the polymerization of tubulin with an IC50 of 0.7 μmol/L, and it also inhibits mitosis in various human tumor cell lines.
Specification
| IUPAC Name | (2S,4S)-2-amino-5-[[(3R,4S,7S,10S,11R)-4-(carboxymethylcarbamoyl)-3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-propan-2-yl-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(15),12(16),13-trien-13-yl]sulfinyl]-4-hydroxypentanoic acid |
| Canonical SMILES | CCC1(C(NC(=O)C(NC(=O)C(C(C2=CC(=C(C=C2S(=O)CC(CC(C(=O)O)N)O)O)O1)O)NC)C(C)C)C(=O)NCC(=O)O)C |
| InChI | InChI=1S/C28H43N5O12S/c1-6-28(4)23(26(41)31-10-19(36)37)33-24(39)20(12(2)3)32-25(40)21(30-5)22(38)14-8-17(45-28)16(35)9-18(14)46(44)11-13(34)7-15(29)27(42)43/h8-9,12-13,15,20-23,30,34-35,38H,6-7,10-11,29H2,1-5H3,(H,31,41)(H,32,40)(H,33,39)(H,36,37)(H,42,43)/t13-,15-,20-,21-,22+,23+,28+,46?/m0/s1 |
| InChI Key | QRLBQXQEGMBXFM-MWFNQMQISA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 1119.5±65.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Ustiloxin A inhibits proliferation of renal tubular epithelial cells in vitro and induces renal injury in mice by disrupting structure and respiratory function of mitochondria
Yongkang Zhang, Qiaolin Xu, Qian Sun, Ren Kong, Hao Liu, Xun'e Yi, Zhengqi Liang, Robert J Letcher, Chunsheng Liu J Hazard Mater. 2023 Apr 15;448:130791. doi: 10.1016/j.jhazmat.2023.130791. Epub 2023 Jan 13.
Recently, we found that Ustiloxin A (UA, a mycotoxin) was widely detected in paddy environment and rice samples from several countries, and was also detected in human urine samples from China. However, the current knowledge about the health risks of UA are limited. In this research, the cytotoxicity of UA in mice renal tubular epithelial cells (mRTECs) was evaluated, and the results indicated that UA arrested cell cycle in G2/M phase via altering cellular morphology and microtubule, and inhibited the proliferation and division of mRTECs. Furthermore, UA could inhibit mitochondrial respiration via binding to the CoQ-binding site in dihydro-orotate dehydrogenase (DHODH) protein, and resulted in mitochondrial damage. These adverse effects of UA on mitochondria might be responsible for the cytotoxicity observed in vitro. In vivo, UA at concentrations that were comparable to the realistic concentrations of human exposure induced renal insufficiency in mice, and this might be associated with the renal mitochondrial damage in mice. However, exposure to UA at those realistic concentrations did not promote the progression from renal insufficiency to renal fibrosis and chronic kidney disease was not observed in mice.
2. Ustiloxin A is Produced Early in Experimental Ustilaginoidea virens Infection and Affects Transcription in Rice
Zheng Hu, Lu Zheng, Junbin Huang, Ligang Zhou, Chunsheng Liu, Hao Liu Curr Microbiol. 2020 Oct;77(10):2766-2774. doi: 10.1007/s00284-020-02072-6. Epub 2020 Jun 11.
Ustiloxin is a kind of 13-membered cyclic peptides found in mature rice false smut generated by Ustilaginoidea virens infecting rice spikelet. So far, six kinds of ustiloxins have been identified from false smut balls (FSBs) in which ustiloxin A is the main component. The toxins can not only inhibit the growth of rice, wheat, and corn, but also poison people and animals. However, so far, there have been few studies of the content of ustiloxin except that in mature FSB. The effect of ustiloxins on the process of infection has not been clarified. In this study, the technique of artificial inoculation coupled with UPLC-ESI-MS was introduced to investigate the content of ustiloxins in the course of infection. The initial formation time of ustiloxin A, B, C, D, F, and G was no later than 5, 5, 9, 7, 7, and 9 days post inoculation (dpi) prior to FSB's formation, respectively. The content of ustiloxin A per spikelet was increased rapidly from 6.0 ng at 5 dpi to 14,157.1 ng at 25 dpi. Meanwhile, the content of ustiloxin A per dry weight (DW) of the FSBs also peaked at 1321.2 μg/g at 25 dpi. Interestingly, both the contents of ustiloxin A per dry weight and per spikelet were significantly reduced from 25 to 30 dpi. Transcriptome sequencing revealed that a total of 146 transcripts (103 upregulated and 43 downregulated) were significantly changed in rice spikelets after 3-h acute exposure to 100 ng ustiloxin A. In addition, several of the significantly altered genes were validated by RT-qPCR.
3. Detection of Ustiloxin A in urine by ultra-high-performance liquid chromatography-tandem mass spectrometry coupled with two-step solid-phase extraction
Qian Sun, Hao Liu, Yongkang Zhang, Ren Kong, Xun'e Yi, Chunsheng Liu J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Sep 1;1181:122916. doi: 10.1016/j.jchromb.2021.122916. Epub 2021 Sep 3.
Due to global outbreak of rice false smut disease, ustiloxin A (UA) was detected in rice. However, accurate methods for monitoring UA in human body fluids were lacking. In this context, a UPLC-MS/MS method based on two-step SPE was constructed for measuring UA in urine. The limits of UA quantification in human and mice urine were 58.3 and 108.7 ng/L, respectively. The proposed method was applied to detect UA in urine samples collected from human and mice. After dietary exposure, the contents of UA in mice urine were from 6.03 to 16.76 μg/g of creatine, accounting for approximate 14% of daily intake dose. Furthermore, due to the trace residues in rice (78-109 ng/kg), no detectable UA was observed in the urine of 20 volunteers. To the best of our knowledge, it is the first time to report the occurrence of UA in mammal urine.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
